Microwave-assisted synthesis of imidazoles: Reaction of p-toluenesulfonylmethyl isocyanide and polymer-bound imines

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 16, 2005, Pages 3717-3719

  Samanta, Swapan K ^a   Kylänlahti, Irene ^a   Yli Kauhaluoma, Jari ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

1,3 Dipolar cycloaddition reaction; Imidazole; Microwave assisted synthesis; Solid phase synthesis; TOSMIC

Indexed keywords

IMIDAZOLE DERIVATIVE; IMINE; TOLUENE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; REACTION ANALYSIS; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

CYCLIZATION; IMIDAZOLES; IMINES; MICROWAVES; MOLECULAR STRUCTURE; NITRILES; POLYMERS; TOSYL COMPOUNDS;

EID: 22844453040     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.05.066     Document Type: Article

References (27)

1. D. Lednicer, and L.A. Mitscher Organic Chemistry of Drug Synthesis Vol. 1 1977 Wiley Interscience New York 226
2. W.J. Greenlee, and P.K.S. Siegl Annu. Rep. Med. Chem. 27 1992 59
3. S.C. Shilcrat, M.K. Mokhallalati, J.M.D. Fortunak, and L.N. Pridgen J. Org. Chem. 62 1997 8449
4. J.P. Rizzi, A.A. Nagel, T. Rosen, S. McLean, and T. Seeger J. Med. Chem. 33 1990 2721
5. G. Shapiro, and B. Gomez-Lor J. Org. Chem. 59 1994 5524
6. J.L. Adams, J.C. Boehm, S. Kassis, P.D. Gorycki, E.F. Webb, R. Hall, M. Sorenson, J.C. Lee, A. Ayrton, D.E. Griswold, and T.F. Gallagher Bioorg. Med. Chem. Lett. 8 1998 3111
7. W.H. Beggs, F.A. Andrews, and G.A. Sarosi Life Sci. 28 1981 111
8. J.N. Delgado, and W.A. Remers 10th ed. Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry 1998 Lippincott-Raven Philadelphia, New York
9. S.V. Ley, and I.R. Baxendale Nat. Rev. Drug Discov. 1 2002 573
10. A. Lew, P.O. Krutzik, M.E. Hart, and A.R. Chamberlin J. Comb. Chem. 4 2002 95
11. P. Lidström, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
12. A. Stadler, and C.O. Kappe J. Comb. Chem. 3 2001 624
13. B.L. Hayes Microwave Synthesis: Chemistry at the Speed of Light 2002 CEM Publishing Matthews, NC
14. I.R. Baxendale, A.-L. Lee, and S.V. Ley J. Chem. Soc., Perkin Trans. 1 2002 1850
15. N.E. Leadbeater, and M. Marco Angew. Chem. Int. Ed. 42 2003 1407
16. I.R. Baxendale, T.D. Davidson, S.V. Ley, and R.H. Perni Heterocycles 60 2003 2707
17. D. Ranganathan, and R. Rathi Tetrahedron Lett. 27 1986 2491
18. S. Sarshar, D. Siev, and A.M.M. Mjalli Tetrahedron Lett. 37 1996 835
19. M.T. Bilodeau, and A.M. Cunningham J. Org. Chem. 63 1998 2800
20. A.M. van Leusen, J. Wildeman, and O.H. Oldenziel J. Org. Chem. 42 1977 1153
21. Ameba resin-PS-MB-CHO, Sigma-Aldrich, catalog no. 51, 644.
22. W. Yihan, and S.R. Wilson Tetrahedron Lett. 38 1997 4021
23. R.L. Shriner, R.C. Fuson, D.Y. Curtin, and T.C. Morrill The Systematic Identification of Organic Compounds 1980 John Wiley & Sons New York pp 162-163
24. TM EXP from Biotage. Reactions were carried out in their proprietary 2-5 mL sealed vials. Caution! Certain isonitriles are unstable at temperatures above 80°C. Therefore, care should be taken when using these compounds as reagents at higher reaction temperatures.
25. ++ H] 311.
26. J. Sisko, M. Mellinger, P.W. Sheldrake, and N.H. Baine Tetrahedron Lett. 37 1996 8113
27. N. Nakajima, R. Abe, and O. Yonemitsu Chem. Pharm. Bull. 36 1988 4244